Methylamine → tert-Butyl 2-oxo-2-(4-morpholin-4-ylphenyl)ethyl(methyl)carbamate

HRID 23713

Reaktionsgleichung

Reaktionsgleichung von HRID 23713
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1)=[O:4].[CH3:17][NH2:18].[C:19](=[O:30])(OC(C)(C)C)[O:20][C:21]([CH3:24])([CH3:23])[CH3:22]>C1COCC1>[O:4]=[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1)[CH2:2][N:18]([CH3:17])[C:19](=[O:30])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22]

Komponenten

5

Edukt 3

HCID 6329MethylamineHCID 27953572-Bromo-1-(4-morpholinophenyl)ethanoneHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Produkt 1

HCID 22574343tert-Butyl 2-oxo-2-(4-morpholin-4-ylphenyl)ethyl(methyl)carbamateAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2-Bromo-1-(4-morpholin-4-ylphenyl)ethanone (Tetrahedron Letters; 39, (1998), 4987-4990)(3.40 g, 11.97 mmol) was dissolved in dry THF (30 ml) under N2 and cooled in ice. A 2M solution of methylamine in THF (12 ml, 24 mmol) was added and the reaction stirred for 1 hr. The mixture was filtered and the filtrate treated with di-t-butyl carbonate (2.61 g, 12 mmol) at ice temperature. Stirring was continued for 24 hr then the solvent evaporated. Chromatography of the residue over silica gel (500 g) eluting with 1% MeOH-1% Et3N-EtOAc gave the product as a pale yellow solid (1.53 g, 38%): mp87-89°.

Aufarbeitung

  1. temperaturecooled in ice
  2. filtrationThe mixture was filtered
  3. stirringStirring
  4. waitwas continued for 24 hr
  5. customthe solvent evaporated
  6. washChromatography of the residue over silica gel (500 g) eluting with 1% MeOH-1% Et3N-EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-14a1a40fce874bbd8bc183963b270f71
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852731B2

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